Benzyl Bromide → 1-Benzyl-4-hydroxy-3-nitropyridin-2(1H)-one

HRID 2244796Notes

Reaction equation

HRID 2244796 reaction equation
[N+:1]([C:4]1[C:5]([OH:11])=[N:6][CH:7]=[CH:8][C:9]=1[OH:10])([O-:3])=[O:2].[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C>[CH2:14]([N:6]1[CH:7]=[CH:8][C:9]([OH:10])=[C:4]([N+:1]([O-:3])=[O:2])[C:5]1=[O:11])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178526878HCID 178526878, compound

Product 1

HCID 587884461-Benzyl-4-hydroxy-3-nitropyridin-2(1H)-oneYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-nitro-pyridine-2,4-diol (5.0 g, 32.3 mmol) in DMF (50 mL) at 0° C. was added NaH (2.6 g, 64.0 mmol 60% in mineral oil). After stirring at 0° C. for 15 min, benzyl bromide (6.03 g, 35.2 mmol) was added and the reaction was stirred at 55° C. for 17 h. The mixture was cooled to room temperature, poured into ice water, and filtered to remove insoluble material. The filtrate was acidified with 1 N HCl, extracted with CH2Cl2, dried with MgSO4, and concentrated. The product was washed with EtOH to give 1-benzyl-4-hydroxy-3-nitro-1H-pyridine-2-one (3.30 g, 42% yield). 1H-NMR (DMSO): δ 7.90 (d, 1H, J=7.6 Hz), 7.27-7.38 (m, 5H), 6.12 (d, 1H, J=7.6 Hz), 5.08 (s, 2H). MS: calculated for C12H10N2O4+H 247.1; found: 247.2.

Workup

  1. stirringthe reaction was stirred at 55° C. for 17 h
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered
  4. customto remove insoluble material
  5. extractionextracted with CH2Cl2
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated
  8. washThe product was washed with EtOH

Sources & evidence

ORD record
ord-3900a28e949c42ae94912621da78131f
Source dataset
uspto-grants-2010_03
Patent number
US07678909B1

Reaction notes

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